Role Description Postmedia has spent over 100 years building Canada’s most trusted media brands. Today, we are leveraging that authority to build the country’s most sophisticated digital sales engine. We are looking for an Associate Account Executive who is driven, coachable, and eager to build a long-term career in digital media sales. This role is designed for high-potential sellers who want to develop into full-cycle Account Executives within a high-performance, tech-enabled environment. You will focus on new business acquisition while being supported by SDRs, and an AI-powered sales tech stack that enables you to sharpen your skills and accelerate your growth. What You’ll Do - Prospect and engage new business through outbound outreach, digital engagement, and SDR-supported opportunities - Conduct virtual discovery calls to identify client needs and qualify opportunities - Present tailored digital advertising solutions across SEO, SEM, Programmatic, Social, and Display - Manage a structured pipeline within CRM, maintaining accurate forecasting and activity tracking - Leverage AI tools to improve call performance, objection handling, and follow-up efficiency - Consistently achieve or exceed revenue and activity targets - Transition qualified opportunities smoothly to internal teams for fulfillment Qualifications - Aspiring Digital Closer: Motivated by new business acquisition and desire to build mastery in consultative digital sales - Tech-Forward: Embrace CRM systems, AI tools, and virtual selling environments as competitive advantages - Highly Coachable: Actively seek feedback and apply coaching insights to continuously improve performance - Performance-Driven: Goal-oriented, resilient, and motivated by uncapped earning potential - B2B Sales Foundation: Experience in sales, lead generation, or client-facing roles; comfortable conducting professional conversations over phone and video Compensation - Pay Rate: $40,000 - $50,000 + uncapped variable compensation - Health & Dental Benefits - Pension Matching - 3 weeks vacation Benefits - Health & Dental Benefits - Pension Matching - 3 weeks vacation

• Outbound Calling: Consistently make a high volume of outbound calls to generate leads and book appointments. • Lead Qualification: Quickly assess potential customers' needs and qualify them for our travel packages. • Sales Presentations: Deliver compelling product presentations over the phone. • Overcoming Objections: Masterfully handle objections and challenges to close deals. • Sales Quotas: Consistently exceed ambitious sales targets and KPIs. • Customer Focus: Build strong relationships with customers and provide exceptional service.

Role Description This is a true enterprise, full-cycle Account Executive role reporting directly to the founder. You will sell into large brokerages, carriers, wirehouses, and adjacent financial services institutions, sourcing your own opportunities, running demos, and closing complex deals. New reps typically start with low-to-mid six-figure deals and graduate to higher ACV as they ramp. - Own the full sales cycle, from sourcing and prospecting through demo and close - Sell into enterprise brokerages, carriers, wirehouses, and large financial institutions - Build and nurture relationships across a relationship-driven market - Run discovery and product demonstrations for a complex platform - Partner with marketing and customer success to identify and win the right accounts Qualifications - 7-15 years of enterprise B2B software sales experience with a track record of larger deals - Demonstrated success at startups, ideally selling into old-school industries - Strong hunter mentality with velocity, energy, and drive - Excellent relationship-building skills - Comfort with technology and AI tools - Bonus: direct experience selling into insurance or financial services Company Description Our partner is a Series A, AI-native platform transforming revenue and commission operations for the insurance and broader financial services industry. They have raised over $12 million, generate millions in annual recurring revenue, and reached that scale in roughly 18 months. Their ambition is to become the operating system for insurance brokerages, agencies, and carriers, selling into an old-school industry hungry for modern, AI-powered tools.

Role Description This is a full-stack mid-market AE role reporting directly to the founder. You will own deals end to end, working inbound demos (roughly 50-60% of revenue), hunting new logos, and representing the company at trade shows. The internal tools and pipeline systems are already in place. You will sell into companies doing $10M-$150M in revenue, with ACVs in the mid-five to low-six figures and roughly one-month sales cycles. - Own the full sales cycle, from inbound demos and discovery through negotiation and close - Hunt for new logos and build relationships across the home services industry - Run discovery and product demos without sales engineer support - Attend trade shows and industry events to source and advance opportunities - Leverage existing tools and pipeline to generate additional pipeline - Consistently manage deals end to end Qualifications - A track record of crushing it as an SDR/BDR ready to step into an AE seat, or founding/early AE experience - A winning mindset, resourcefulness, and an owner's mentality - Hunger, ambition, coachability, and curiosity - Comfortable in a fast-moving startup environment - Bonus: 1-2 years closing multi-stakeholder deals, or a competitive-arena background Company Description Our partner builds AI agents for blue-collar home services industries, including HVAC, plumbing, roofing, flooring, and home remodeling, a roughly $1 trillion market. Their suite of AI agents spans the full customer journey, from real-time sales coaching for reps in the field to voice agents that handle inbound calls. The company is bootstrapped, profitable, and went from zero to seven figures in revenue in about nine months, with sights set on 10x growth this year.